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Search results; Over 1,000 homes in Monterey

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Top guest favourite
Cabin in Monterey
Amazing Berkshire Mountains Cabin
4 bedrooms, 4 beds, 2 private bathrooms
25–30 Oct
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4.95 out of 5 average rating, 313 reviews
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Superhost
Home in Monterey
Forget-Me-Not by AvantStay | Bold Lakefront Escape
4 bedrooms, 8 beds, 4 bathrooms
8–13 Nov
4.9 out of 5 average rating, 71 reviews
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Top guest favourite
Cottage in Monterey
Beaver Lodge
3 bedrooms, 3 queen beds, 1.5 bathrooms
14–19 Oct
5.0 out of 5 average rating, 84 reviews
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Top guest favourite
Home in Monterey
Jaw dropping mountain & lake views
4 bedrooms, 4 beds, 2 bathrooms
1–6 Nov
4.96 out of 5 average rating, 311 reviews
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Top guest favourite
Home in Monterey
Contemporary Modern Mountain Retreat
4 bedrooms, 8 beds, 3 bathrooms
5–10 Oct
5.0 out of 5 average rating, 8 reviews
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Top guest favourite
Home in Monterey
Berkshires Retreat | Fall Foliage | Fenced Yard
5 bedrooms, 7 beds, 3.5 bathrooms
11–16 Oct
5.0 out of 5 average rating, 50 reviews
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Home in Monterey
Monterey Home w/ Hot Tub, Pool & Game Room!
6 bedrooms, 10 beds, 6 bathrooms
7–12 Dec
4.85 out of 5 average rating, 47 reviews
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Guest favourite
Home in Monterey
Direct on Lake Garfield: Book Fall Weekends!
3 bedrooms, 5 beds, 3.5 bathrooms
24–29 Oct
4.96 out of 5 average rating, 23 reviews
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Guest favourite
Home in Monterey
Forest Hollow | Waterfront • Kayaks • Wood Stove
3 bedrooms, 4 beds, 1.5 bathrooms
8–13 Oct
4.86 out of 5 average rating, 104 reviews
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Superhost
Cabin in Monterey
Secluded cabin with babbling brook
3 bedrooms, 3 beds, 1 bathroom
17–22 Nov
4.87 out of 5 average rating, 259 reviews
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Cabin in Monterey
Exotic Mountain Retreat in the Berkshires.
5 bedrooms, 9 beds, 4.5 bathrooms
8–13 Oct
4.89 out of 5 average rating, 209 reviews
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Guest favourite
Home in Monterey
Garfield Grounds | Lakeside • Guest Cottage • Dock
4 bedrooms, 5 beds, 3 bathrooms
12–17 Oct
4.93 out of 5 average rating, 29 reviews
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Top guest favourite
Home in Monterey
Quiet Retreat on Five Acres w/views
4 bedrooms, 4 beds, 4 bathrooms
26–31 Oct
5.0 out of 5 average rating, 17 reviews
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Superhost
Home in Monterey
Stone Tudor in Monterey Village
3 bedrooms, 3 beds, 3 bathrooms
1–6 Oct
4.71 out of 5 average rating, 97 reviews
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Superhost
Home in Monterey
Dog-Friendly Berkshires Retreat w/Fenced Yard
3 bedrooms, 3 beds, 2.5 bathrooms
11–16 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Monterey
Tranquility and Beauty at Lake Haven
3 bedrooms, 5 beds, 2 bathrooms
21–26 Jun
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Home in Monterey
Charming cottage w/ gorgeous views.
2 bedrooms, 2 beds, 2 bathrooms
12–17 Nov
4.93 out of 5 average rating, 374 reviews
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Guest favourite
Home in Monterey
Bidwell Landing | Lakefront • Spacious
4 bedrooms, 5 beds, 3 bathrooms
25–30 Oct
4.88 out of 5 average rating, 112 reviews
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Top guest favourite
Home in Great Barrington
Fall Weekends, Lake Buel Dock Sunsets: Sleeps 8!
4 bedrooms, 5 beds, 2 bathrooms
11–16 Oct
4.95 out of 5 average rating, 40 reviews